Methylmercaptan sodium → HCID 19747280, compound

HRID 484308Notes

Reaction equation

HRID 484308 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[O:16])[C:10]3[NH:11][CH2:12][CH:13]=[CH:14][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:17]=1.[Na].[CH3:19][SH:20]>CN(C)C=O>[CH3:19][S:20][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[O:16])[C:10]3[NH:11][CH2:12][CH:13]=[CH:14][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 45051789Methylmercaptan sodiumHCID 67714904HCID 67714904, compound

Product 1

HCID 19747280HCID 19747280, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Chloro-5,6-dihydro-1H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (3.5 g) was dissolved in 60 ml of dimethylformamide, followed by the addition of 13.4 g of a 15% aqueous solution of methyl mercaptan sodium salt. The resultant mixture was refluxed for 14 hours. The reaction mixture was cooled and then concentrated under reduced pressure. Water was added to the residue, followed by extraction with methylene chloride. The resulting extract was washed with a brine, dried over anhydrous MgSO4 and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column and relevant chloroform eluate fractions were concentrated. The residue was recrystallized from toluene, whereby 3.57 g of 8-methylthio-5,6-dihydro-1H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one were obtained (yield: 97%). 2.50(3H,s), 3.16(4H,s), 7.00-7.52(3H,m), 7.66(1H,dd), 8.12(1H,d), 8 72(1H,dd).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionfollowed by extraction with methylene chloride
  5. extractionThe resulting extract
  6. washwas washed with a brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by chromatography on a silica gel column and relevant chloroform eluate fractions
  11. concentrationwere concentrated
  12. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-9846f774bb9546e1afded09ceb3fd80c
Source dataset
uspto-grants-1993_07
Patent number
US05231101

Reaction notes

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